K-858
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MedKoo CAT#: 407309

CAS#: 72926-24-0

Description: K-858 is a novel inhibitor of mitotic kinesin Eg5 and antitumor agent, induces cell death in cancer cells. K858 blocked centrosome separation, activated the spindle checkpoint, and induced mitotic arrest in cells accompanied by the formation of monopolar spindles. Long-term continuous treatment of cancer cells with K858 resulted in antiproliferative effects through the induction of mitotic cell death, and polyploidization followed by senescence. K858 exhibited potent antitumor activity in xenograft models of cancer, and induced the accumulation of mitotic cells with monopolar spindles in tumor tissues.

Chemical Structure

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K-858
CAS# 72926-24-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407309
Name: K-858
CAS#: 72926-24-0
Chemical Formula: C13H15N3O2S
Exact Mass: 277.09
Molecular Weight: 277.342
Elemental Analysis: C, 56.30; H, 5.45; N, 15.15; O, 11.54; S, 11.56

Price and Availability

Size Price Availability Quantity
10mg USD 150
25mg USD 250
50mg USD 450
100mg USD 650
200mg USD 850
500mg USD 1850
1g USD 2950
2g USD 3950
5g USD 6550
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Synonym: K-858; K 858; K858.

IUPAC/Chemical Name: N-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide

InChi Key: JEFVYQYZCAVNTP-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H15N3O2S/c1-9(17)14-12-15-16(10(2)18)13(3,19-12)11-7-5-4-6-8-11/h4-8H,1-3H3,(H,14,15,17)

SMILES Code: CC(NC1=NN(C(C)=O)C(C2=CC=CC=C2)(C)S1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: K858 Racemic is an ATP-uncompetitive inhibitor of kinesin Eg5 with an IC50 of 1.3 μM.
In vitro activity: K858 inhibited cell replication by rendering cells incapable of developing normal bipolar mitotic spindles. At the same time, K858 blocked the cell cycle in the G2 phase and induced the accumulation of cytoplasmic cyclin B and, eventually, apoptosis. Additionally, K858 inhibited cell migration and attenuated the malignant phenotype. Reference: Invest New Drugs. 2022 Jun;40(3):556-564. https://pubmed.ncbi.nlm.nih.gov/35312942/
In vivo activity: K858 exhibited potent antitumor activity in xenograft models of cancer, and induced the accumulation of mitotic cells with monopolar spindles in tumor tissues. Importantly, K858, unlike antimicrotubule agents, had no effect on microtubule polymerization in cell-free and cell-based assays, and was not neurotoxic in a motor coordination test in mice. Taken together, the Eg5 inhibitor K858 represents an important compound for further investigation as a novel anticancer therapeutic. Reference: Cancer Res. 2009 May 1;69(9):3901-9. https://pubmed.ncbi.nlm.nih.gov/19351824/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 90.14
DMSO 61.7 222.35
DMSO:PBS (pH 7.2) (1:4) 0.2 0.72
Ethanol 4.0 14.42

Preparing Stock Solutions

The following data is based on the product molecular weight 277.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Nicolai A, Taurone S, Carradori S, Artico M, Greco A, Costi R, Scarpa S. The kinesin Eg5 inhibitor K858 exerts antiproliferative and proapoptotic effects and attenuates the invasive potential of head and neck squamous carcinoma cells. Invest New Drugs. 2022 Jun;40(3):556-564. doi: 10.1007/s10637-022-01238-2. Epub 2022 Mar 21. PMID: 35312942; PMCID: PMC9098576. 2. Marconi GD, Carradori S, Ricci A, Guglielmi P, Cataldi A, Zara S. Kinesin Eg5 Targeting Inhibitors as a New Strategy for Gastric Adenocarcinoma Treatment. Molecules. 2019 Oct 31;24(21):3948. doi: 10.3390/molecules24213948. PMID: 31683688; PMCID: PMC6864856. 3. Nakai R, Iida S, Takahashi T, Tsujita T, Okamoto S, Takada C, Akasaka K, Ichikawa S, Ishida H, Kusaka H, Akinaga S, Murakata C, Honda S, Nitta M, Saya H, Yamashita Y. K858, a novel inhibitor of mitotic kinesin Eg5 and antitumor agent, induces cell death in cancer cells. Cancer Res. 2009 May 1;69(9):3901-9. doi: 10.1158/0008-5472.CAN-08-4373. Epub 2009 Apr 7. PMID: 19351824.
In vitro protocol: 1. Nicolai A, Taurone S, Carradori S, Artico M, Greco A, Costi R, Scarpa S. The kinesin Eg5 inhibitor K858 exerts antiproliferative and proapoptotic effects and attenuates the invasive potential of head and neck squamous carcinoma cells. Invest New Drugs. 2022 Jun;40(3):556-564. doi: 10.1007/s10637-022-01238-2. Epub 2022 Mar 21. PMID: 35312942; PMCID: PMC9098576. 2. Marconi GD, Carradori S, Ricci A, Guglielmi P, Cataldi A, Zara S. Kinesin Eg5 Targeting Inhibitors as a New Strategy for Gastric Adenocarcinoma Treatment. Molecules. 2019 Oct 31;24(21):3948. doi: 10.3390/molecules24213948. PMID: 31683688; PMCID: PMC6864856.
In vivo protocol: 1. Nakai R, Iida S, Takahashi T, Tsujita T, Okamoto S, Takada C, Akasaka K, Ichikawa S, Ishida H, Kusaka H, Akinaga S, Murakata C, Honda S, Nitta M, Saya H, Yamashita Y. K858, a novel inhibitor of mitotic kinesin Eg5 and antitumor agent, induces cell death in cancer cells. Cancer Res. 2009 May 1;69(9):3901-9. doi: 10.1158/0008-5472.CAN-08-4373. Epub 2009 Apr 7. PMID: 19351824.

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1: Indorato RL, DeBonis S, Kozielski F, Garcia-Saez I, Skoufias DA.
STLC-resistant cell lines as tools to classify chemically divergent Eg5 targeting
agents according to their mode of action and target specificity. Biochem
Pharmacol. 2013 Nov 15;86(10):1441-51. doi: 10.1016/j.bcp.2013.09.003. Epub 2013
Sep 13. PubMed PMID: 24041742.


2: Nakai R, Iida S, Takahashi T, Tsujita T, Okamoto S, Takada C, Akasaka K,
Ichikawa S, Ishida H, Kusaka H, Akinaga S, Murakata C, Honda S, Nitta M, Saya H,
Yamashita Y. K858, a novel inhibitor of mitotic kinesin Eg5 and antitumor agent,
induces cell death in cancer cells. Cancer Res. 2009 May 1;69(9):3901-9. doi:
10.1158/0008-5472.CAN-08-4373. Epub 2009 Apr 7. PubMed PMID: 19351824.